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<h1><a href="https://archiveofourown.org/works/27876030">Next Time, I'll Keep You</a> by <a class='authorlink' href='https://archiveofourown.org/users/Kleineganz/pseuds/Kleineganz'>Kleineganz</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>Next Time... [2]</td></tr>

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Alternate Universe - Canon Divergence, Anal Plug, Anal Sex, Belting, Coming Untouched, Dubious Consent, M/M, Non-Consensual Spanking, Pining, Power Imbalance, Team Dean Winchester's Red Ass</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-12-04</td></tr>

<tr><td><b>Updated:</b></td><td>2020-12-04</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-10 14:40:10</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>Creator Chose Not To Use Archive Warnings</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,874</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/27876030</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/Kleineganz/pseuds/Kleineganz</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>It's been nearly a year since Dean Winchester was raped by Sheriff Castiel Novak over the hood of his police cruiser. So, why does Dean have to jerk off every time he thinks about that night?</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester</td></tr>

<tr><td><b>Series:</b></td><td>Next Time... [2]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/2040978</td></tr>

<tr><td><b>Comments:</b></td><td>11</td></tr>

<tr><td><b>Kudos:</b></td><td>147</td></tr>

</table>

<a name="section0001"><h2>Next Time, I'll Keep You</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>It’s been almost a year since Dean was taken … no, <em>raped</em> … by Sheriff Novak. Yet, nothing he did could get the sheriff out of his head. Every time Dean jacked off in the shower, his mind went back to when he was bent over the sheriff’s car, hands cuffed behind him, and fucked against his will. Fucked until he’d had the best damn orgasm of his life.</p><p>Ever since that night, Dean’s been chasing that high. He’d tried fucking himself with dildos, vibrators, even prostate massagers. They all felt great, but he couldn’t achieve the same level of orgasmic transcendence.</p><p>Out of desperation, Dean even let a few dudes fuck him in the back alleys behind bars, taking him roughly as he held himself up against a wall. That was better than the toys, but still not enough. <em>What was it about that sheriff?</em></p><p>Now Dean found himself about an hour outside of bumfuck nowhere, staring at the calling card the sheriff had shoved into his pocket the year before. <em>Castiel Novak, Sheriff. Next time you’re in town, call me. 555-867-5309.</em></p><p>As soon as he’d fished the card out of his wallet, his dick twitched with anticipation. <em>Fuck, I can’t believe I’m doing this</em>, he chastised himself as he fished his phone out of his pocket and dialed the number.</p><p>***</p><p>About an hour later, Dean was driving slowly down an old sideroad that looked like it was never used. His heart raced in his chest, and his dick was already hard as a rock. It had been ever since he’d heard that sheriff’s gravelly voice over the phone.</p><p>Next thing he knew, the sheriff’s car showed up out of nowhere behind him, lights flashing and siren blaring in the stillness. Dean almost came in his jeans just at the sight. <em>Fuck</em>.</p><p>Pulling over and turning off the engine, Dean waited. The sheriff sauntered over with a smug look on his face. “License and registration, please.”</p><p><em>So, we’re doing this now?</em> Dean thought as he played along.</p><p>Handing them over to Sheriff Novak, Dean couldn’t help but notice the enticing bulge in the sheriff’s slacks. Dean’s dick twitched again, and he knew he was soaking through the front of his jeans by now.</p><p>“Dean Winchester, eh?” the sheriff remarked. “Didn’t I tell you last time never to come back?”</p><p>“Yes, sir. I was only passing through this time. I hadn’t planned on stopping,” Dean lied.</p><p>“Please step out of the vehicle,” Sheriff Novak ordered, pocketing Dean’s license and registration. “I’ll hang on to these for now.”</p><p>Slowly, Dean opened the door of his beloved Impala and stepped out. Once he was standing and had closed the door, the sheriff grabbed Dean, pulling his arms behind his back, and cuffing them. “Right this way.”</p><p>Sheriff Novak held Dean’s upper arm in an iron grip as he marched him around to the back of his car, forcefully bending him over the trunk. “You’re a stubborn one, aren’t you, pretty boy?” he asked as he reached around and pulled Dean’s belt free from his jeans before opening his fly and forcing Dean’s jeans and boxers down to his ankles.</p><p><em>Just like the last time,</em> Dean shuddered in anticipation.</p><p>“What have we here?” the sheriff asked as he spread apart Dean’s ass cheeks. The plug he’d slipped into his ass this morning must have been clearly visible. A rough, dry hand cupped his ass cheek and then slipped over his hip and reached around, stroking Dean’s hard-as-nails cock. The sheriff leaned close and growled into his ear. “You already this hard for me, pretty boy?”</p><p>All Dean could do was whine in response, his face heating at the humiliation of having to admit he wanted this. No, he <em>needed</em> it.</p><p>“First, you need to be taught a lesson,” the sheriff declared, as he took a step back from Dean. “When I tell you to leave and never come back, you ought to listen. Seems I need to whip some sense into you.”</p><p>Without warning, the sheriff whipped Dean’s ass with his own belt. The hits came fast and hard, making Dean howl. When Sheriff Novak paused, he grabbed Dean by the hair. “Are you sorry you came back, yet?”</p><p>Dean was conflicted. His dick was completely on-board with his ass getting whipped, but his ass was definitely protesting. Tears of frustration welled in his eyes as he didn’t know how to reply.</p><p>“I guess you haven’t learned your lesson yet, pretty boy. You’re getting whipped until you apologize for disobeying me.”</p><p>The belt seared welts into Dean’s skin over and over as the sheriff peppered his ass and thighs with lash after lash. Eventually, the damn broke inside Dean and he cried out for mercy. “I’m sorry! Please, stop. I’m so sorry.”</p><p>Hearing the belt get tossed aside, Dean breathed a sigh of relief. He took a long, shuddering breath, trying to stop himself from sobbing like a baby.</p><p>“That’s more like it,” the sheriff said, pulling Dean upright, turning him and pushing him down until the dirt and gravel dug painfully into his knees. Looking up at the sheriff, he watched as the man opened his fly and pulled out his rock-hard cock. “Now, be a good boy and get my cock nice and wet. If I feel teeth, you’ll earn yourself another sound whipping, do you understand?”</p><p>Nodding, Dean obediently opened his mouth. Slowly the cock was pushed deep into Dean’s mouth and down his throat. Remaining still, Dean let the man use his throat, doing his best to cover his teeth to avoid another punishment.</p><p>“Your lips look so good wrapped around my dick, I’m almost tempted to just blow my load down your throat,” the sheriff said as he pulled his cock out. “But I can’t deprive myself of enjoying that delicious ass of yours again.”</p><p>Pulling Dean back onto his feet, he was once again bent over the trunk of his car. His plug was pulled out, and while one hand gripped his hip tight, the sheriff began feeding his dick into Dean’s prepared hole. It didn’t hurt going in nearly as much as it had the first time the sheriff had taken him.</p><p>“Fuck, you’re still as tight as a virgin, pretty boy,” the sheriff grunted as he hilted himself inside Dean.</p><p>Not slowing down to let Dean adjust, the sheriff began to pound his ass hard, and Dean transcended into ecstasy. <em>Fuck, what is it about this guy’s dick that feels so fucking perfect?</em></p><p>Dean moaned at every thrust as the sheriff grabbed Dean’s cuffed arms for leverage, letting him pound even harder into Dean, slamming against his flaming backside and sparking a perfect mix of pain and pleasure.</p><p>When Dean tried to buck back and meet the man’s thrusts, he was given a sharp spank on his thigh. “Stay still and take your fucking like a good boy.”</p><p>Dean’s cock was aching, and he did his best to relax and let himself be used, hoping the sheriff would help tip him over the edge with that firm grip of his. Blanketing Dean’s back, the sheriff rutted into him with deep jabs of his hips, aiming for his prostate each time. “If you want to come, you have to do it untouched. I’m not going to help a disobedient boy, and I want you to come from getting fucked by my cock. Can you do that for me, pretty boy?”</p><p>Whining and shaking his head, Dean wasn’t sure. He’d never come untouched before, but he was so damn close. The sheriff kept nailing Dean in that one perfect spot. Then he reached up and grabbed Dean’s shoulders so he could push in even deeper, before beginning a litany of dirty talk.</p><p>“You love being filled up with my cock, don’t you, pretty boy? You take it so well. Have you been aching to have me inside you again all this time? I bet you have. You’re such a slut for my cock now, aren’t you? I bet you’d love it if I just chained you up and used you as my personal fuck toy, wouldn’t you?”</p><p>Between the angle of the thrusts and the filthy images his mind was conjuring from the sheriff’s words, Dean’s pleasure reached a breaking point as it spiraled out of control. His orgasm blindsided him, coursing through him as he bucked and shuddered, his dick shooting streams of cum all over the ground and the back of the Impala.</p><p>When Dean came back to himself, the sheriff was upright again, pounding into his ass earnestly. Now oversensitive, Dean whimpered as the continued fucking prolonged his orgasm, his dick valiantly trying to pump out more semen.</p><p>“I knew you could come untouched on my cock,” the sheriff grunted. “Now I’m going to fill you up good, and come so deep, it’ll still be dripping out of you next week.”</p><p>With an iron grip on his hip and shackled arms, the sheriff pulled Dean back onto his cock hard, while fucking into him a dozen more times before stuttering to a stop and groaning in ecstasy. “That’s it … fucking take it,” the sheriff growled as Dean felt his ass fill with spurt after spurt of the sheriff’s seed.</p><p>Breathing heavily, the sheriff blanketed Dean’s back and kept his cock nestled in Dean’s ass until it was too soft, and it slipped free. “You’re such a good fuck, pretty boy. It’s almost a shame to send you on your way.”</p><p>With that, the man stood up, pushing Dean’s plug back into his hole. Then he pulled Dean up on wobbling legs and once again pushed him to his knees. “You know what to do,” the sheriff said, waving his soft dick in Dean’s face. Rolling his eyes, Dean leaned forward and did his best to lick the sheriff’s cock clean. Thankfully, this time the man did not ask him to lick his spend from the side of the car.</p><p>Once he was done, the sheriff tucked himself away before he helped Dean back to his feet, and the sheriff helped him pull up his boxers and jeans and hung Dean’s belt over his shoulders. Then he escorted Dean back toward the front of his car and uncuffed him. “Now, let this be a final warning to you. You don’t want to find out what happens next time, if I ever catch you in these parts again.”</p><p>The sheriff pulled out Dean’s license, registration, and some folded paper, tucking them into Dean’s shirt pocket. “Now get out of here before I change my mind and arrest you for loitering.”</p><p>***</p><p>Later that night, still enjoying the pleasant ache in his ass, Dean checked into a motel in a town several hours down the highway. Sitting on the single bed, he fished out the paper in his pocket and unfolded it. What it said made his dick twitch again.</p><p>It was a document with a couple of pages. On the front of the first page, the title read “Rules, Rights, and Expectations of Becoming a Kept Boy.” Scrawled under that in what had to be the sheriff’s handwriting was a note.</p><p>
  <em>“The next time I see you again, I’m going to keep you.”</em>
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